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Literature DB >> 21288044

Asymmetric total synthesis of (+)-danicalipin A.

Takehiko Yoshimitsu¹, Ryo Nakatani, Akihiro Kobayashi, Tetsuaki Tanaka.

Abstract

A convergent asymmetric total synthesis of (+)-danicalipin A is accomplished, in which two chlorinated fragments are stereoselectively joined by 1,3-dipolar coupling, leading to the confirmation of the absolute configuration of the natural product.

Mesh：

Substances：
Lipids
danicalipin A

Year: 2011 PMID： 21288044 DOI： 10.1021/ol1029518

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

Keyword Cloud
Cited

16 in total

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors: K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal: Chem Soc Rev Date: 2012-06-28 Impact factor: 54.564

2. Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.

Authors: Jakub Saadi; Matsujiro Akakura; Hisashi Yamamoto
Journal: J Am Chem Soc Date: 2011-08-18 Impact factor: 15.419

3. Synthesis of β-hydroxy-α-haloesters through super silyl ester directed syn-selective aldol reaction.

Authors: Susumu Oda; Hisashi Yamamoto
Journal: Org Lett Date: 2013-11-08 Impact factor: 6.005

4. Approaches to the chemical synthesis of the chlorosulfolipids.

Authors: Won-Jin Chung; Christopher D Vanderwal
Journal: Acc Chem Res Date: 2014-01-08 Impact factor: 22.384

5. Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.

Authors: Matthew L Landry; Dennis X Hu; Grace M McKenna; Noah Z Burns
Journal: J Am Chem Soc Date: 2016-04-08 Impact factor: 15.419

Asymmetric total synthesis of (+)-danicalipin A.

Review 1. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

2. Rapid, one-pot synthesis of β-siloxy-α-haloaldehydes.

3. Synthesis of β-hydroxy-α-haloesters through super silyl ester directed syn-selective aldol reaction.

4. Approaches to the chemical synthesis of the chlorosulfolipids.

5. Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.

Review 6. Catalytic Enantioselective Dihalogenation in Total Synthesis.

7. β-Siloxy-α-haloketones through highly diastereoselective single and double mukaiyama aldol reactions.

8. Triphosgene-pyridine mediated stereoselective chlorination of acyclic aliphatic 1,3-diols.

9. A synthesis of the chlorosulfolipid mytilipin A via a longest linear sequence of seven steps.

10. The Alga Ochromonas danica Produces Bromosulfolipids.